A family of fluorinated azobenzene-based push-pull chromophores with one, two, and three trifluorovinyl ether (TFV) groups in linear and branched architecture was synthesized and utilized as active materials in the low optical loss electrooptic (EO) composites. The fluorinated azobenzene chromophores exhibited increased solubility (30-50 wt %) in semifluorinated polymer host, such as perfluorocyclobutane (PFCB) aromatic ether resin after crosslinking, compared with the commercially available nonfluorinated azobenzene chromophore Disperse Red 1 (1-2 wt %). The impact of this approach on the optical properties on the polymer blends is assessed through optical propagation loss measurements and EO characterization. The resulting fluorinated EO composites showed excellent optical clarity, low birefringence, and low optical loss less than 0.5 dB/cm, while giving EO coefficients of about 3-7 pm/V at 1550 nm. (c) 2007 Wiley Periodicals, Inc.